Boies vs. Olson

A look at the two legal titans behind the Gore and Bush teams.

Topics: 2000 Elections, Microsoft,

David is Bill Gates’ former nemesis; Ted is Bill Clinton’s.

David once was chief counsel and staff director for the Senate antitrust subcommittee, and then the Judiciary Committee, for Sen. Ted Kennedy, D-Mass. Ted served as an assistant attorney general in the Reagan administration and later represented the president during the Iran-Contra scandal.

David wears off-the-rack suits from department stores and scuffed Rockports. His hair is messy, and he wears a $20 Casio wrapped around his shirt sleeve. Ted sports the $1,500 suits he buys at Wilkes Bashford in San Francisco.

High-profile attorneys David Boies and Ted Olson couldn’t have been better cast for their new star appearances. Boies represents Vice President Al Gore, while Olson is adding his expertise to efforts by Gov. George W. Bush in the post-election lawsuits related to the Florida recount. Where these two attorneys come from and the cases they’ve left in their wake reveal at least as much about them as they do about where Florida’s electoral hurricane may end up landing. Their participation in the Florida fracas shows just how determined each side is to outmaneuver the other in the legal rulings that may determine who will be the next president of the United States.

On Saturday evening, neither side was sure who would represent it in the Florida Supreme Court on Monday, but both Boies and Olson have played major roles in all the legal maneuverings to date.

“You’ve got two stars here, I think it’s fair to say,” says Dick Wiley, former director of the Federal Communications Commission and a friend of Olson’s. “They’re both at the top of their profession.”

Rumpled and media savvy, Boies is best known for his role in the Justice Department’s antitrust suit against Microsoft. Gates attacked him personally at one point, saying Boies was “out to destroy Microsoft … and make us look bad.” He has certainly never shied away from attention; he successfully defended CBS from a libel suit brought by Gen. William Westmoreland, and has represented radio talk show host Don Imus, comedian Garry Shandling and Yankees owner George Steinbrenner.

Until this past week, he had never taken a side in such a clearly partisan battle.

The dapper Olson, conversely, is — as he once said jokingly at a meeting of conservative legal organization the Federalist Society — “at the heart” of “the vast right-wing conspiracy.”



One of independent counsel Ken Starr’s best friends, Olson helped ABC News negotiate an interview with Monica Lewinsky, and ran the Arkansas Project — a multimillion-dollar investigation into the life of President Clinton funded by right-wing billionaire Richard Mellon Scaife. And Olson defended controversial Arkansas witness David Hale during the Senate hearings on Whitewater. He has taken on some landmark conservative causes, defending the Virginia Military Institute in its failed attempt to remain all male and successfully representing four white students who sued the University of Texas law school, claiming its affirmative action policy denied them their rightful acceptance by the school. Olson and Boies have yet to square off against each other — and may not. The fight over the validity of the hand recounts is taking two legal paths: Olson is on the federal track while Boies is handling Florida state litigation.

This seems only appropriate considering their respective strengths, though both, in the past couple of days, have suffered legal setbacks.

Members of the Gore team think local attorney Dexter Douglass ably represented them at the trial level. A folksy local attorney, he effused colloquialisms and spoke the judge’s language. Boies was flown in Tuesday night to work on the case as it proceeds up to the appellate and state Supreme Court.

He has “clicked very, very well” with the heads of the Gore recount committee, former campaign chairman Bill Daley and former Secretary of State Warren Christopher, according to a Gore lawyer.

But what does Boies, based in New York, know about Florida law? It doesn’t matter, say his friends. “He’s the best legal mind I know,” declares James Fox Miller, former president of the Florida Bar Association and Boies’ “best friend since four days into Northwestern Law School in 1963.”

Boies’ experience is largely as a trial lawyer, not an appellate one. Then again, Boies had never tried a libel case before the Westmoreland suit, Miller says. But when the case was over, “he was the No. 1 libel lawyer in the country.” Similarly, Miller adds, “he’d never even turned on a computer before the Microsoft case.”

The decision was made to have Boies sit second chair to Douglass on Thursday before Circuit Judge Terry Lewis as they fought Secretary of State Katherine Harris’ announcement Wednesday that she wouldn’t accept any new vote tallies as a result of county hand recounts.

On Friday, Judge Lewis ruled against their argument. The case is not over, and it is now before the Florida Supreme Court. But while it can be argued that Boies brings a certain degree of media savvy to the table, one of his problems may be, according to his critics, that he wages a successful media campaign more than a legal one.

It worked for him in the Microsoft case. But Robert Levy, a senior fellow in constitutional studies at the libertarian Cato Institute, says Boies’ stellar reputation — in naming him 1999 Lawyer of the Year, the National Law Journal called him “the Michael Jordan of the courtroom” — is ill-deserved.

“I think he’s been deified and I think that sort of deification is a bit premature in the Microsoft case, because it’s about to be overturned,” Levy says.

Levy says that Boies’ arguments were over the top for the benefit of the cameras. “The case played to the media. It didn’t focus on substantive legal issues, but instead emphasized the ridicule of both the company and Bill Gates in particular.” While the issues should have been the extent to which Microsoft did or did not have a monopoly, Levy says, “instead what we got was a mouthful of how evil Bill Gates was, a focus on e-mails and conversations between Bill Gates and others in his company.”

That may have been the only way to win the case, Miller says, and Boies can hardly be faulted for pursuing a legal plan that worked, at least in the short term. “When I was asked if I thought David would win the Microsoft case, I said I didn’t know, but that if he can’t win it, it’s not winnable.” The same is true in Tallahassee, Miller argues.

Likewise, if anyone can make Bush’s case, say Olson’s fans, he can. Daniel Troy, a former clerk for Judge Robert Bork, a constitutional lawyer and an associate scholar at the American Enterprise Institute, says, “He is one of the leading — if not the leading — Republican constitutional and appellate lawyers in the country.”

But so far, he has had a tough time of it. On Monday in U.S. District Court in Miami, Olson argued against the recounts on federal grounds before Judge Donald Middlebrooks, a Clinton appointee. He called the hand recount process “selective, standardless, subjective, unreliable and, inevitably, biased.” Middlebrooks ruled against Olson’s motion, and on Friday the 11th Circuit Court of Appeals in Atlanta refused to consider an appeal.

That level of the fight isn’t over, however. As former Secretary of State James Baker, representing Bush, said, the court “specifically noted that we are free to return to the federal court to present our constitutional challenges to the selective and subjective manual recount process at the appropriate time in the future.” On Friday Olson filed papers insisting that the “entire world is witnessing the distortion and destruction of a presidential election in selected areas in Florida.” This may be a losing battle, however; there are surely many conservative lawyers in Washington who think the premise of Olson’s fight — that the federal government would intrude on a local election — goes against conservative legal opinion. So why would he even take this on?

First, Olson is, as Troy says, “sort of a lawyer of the right, clearly a Republican,” not to mention one of the three co-chairmen of Lawyers for Bush-Cheney. Also, Troy says, Olson has “a very profound sense of fair play … Ted is not as predictable as you might think. The left would caricature him as some true-blue conservative, but in his personal style he’s more iconoclastic.”

An example, Troy says, is Olson’s taking up the cause of fighting federal sentencing guidelines in the case of Los Angeles police officer Stacey Koon, one of the cops convicted of violating Rodney King’s civil rights by beating him in March 1991, an argument Olson won before the U.S. Supreme Court in June 1997. On one level, defending a cop is almost always a conservative cause, and defending one of the guys who beat King isn’t exactly left-wing. But federal sentencing guidelines have been a Republican charge for quite some time. So for Olson to have argued that a federal judge was appropriate in deviating from federal sentencing guidelines could be seen as unusual, especially for a lawyer considered by his peers to be a “Borkian originalist,” Troy says.

Even more controversial — in GOP circles, at any rate — was Olson’s defense of New York Newsday reporter Tim Phelps against a special prosecutor hired by the Senate to investigate leaks during the confirmation hearings for then-Supreme Court nominee Clarence Thomas. Phelps broke the story that Thomas had been accused of sexual harassment by law professor Anita Hill.

But Olson’s conservative bone fides are long established; he and his pundit wife, Barbara, who wrote an anti-Hillary Clinton screed called “Hell to Pay,” are beloved members of the Washington right.

“He is good friends with just about everybody,” Troy says, describing a scene this summer when Olson was at a reception for the Reagan Library in Philadelphia during the Republican National Convention.

“Nancy Reagan was whispering things in his ear; Ted was chatting with Pete Wilson here, hugging Rudy Giuliani there,” Troy says. “Everybody likes him, and that’s saying a lot for someone as high profile and successful as he is.”

Well, not everybody, of course. As first reported by Jonathan Broder in Salon in April 1998, being the center of so much conservative energies had some wondering how Olson could possibly represent both Whitewater witness Hale and American Spectator magazine without having a conflict of interest.

And, of course, Olson’s involvement in so many anti-Clinton activities (he even helped Paula Jones’ attorneys practice for their case before the U.S. Supreme Court) raises the thought — in the minds of some Democrats, at least — that Olson’s presence really is evidence of a vast right-wing conspiracy.

Repentant former conservative journalist David Brock, in a 1997 Esquire magazine mea culpa, wrote that he was frozen from the conservative inner circle, and in fact disinvited from an Olson cocktail party, after he wrote a somewhat sympathetic biography of Hillary Clinton.

“He’s very competent, but he’s very right-wing extreme,” says a Democratic strategist. “It appears that the Republicans are employing the same extreme strategies that they’ve tried in the past six years. This kind of partisanship over pragmatism and strong policy has failed them in the past, and we feel it will fail them again in this case.”

Maybe, maybe not. At this point, the only prediction any sane person would make is that both Boies and Olson are able lawyers. And while no one wants the endless Florida legal wrangling to continue, their participation offers the possibility of at least one payoff for observers: a true clash of the titans.

Jake Tapper is the senior White House correspondent for ABC News.

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